Filmmaker Ken Fisher was preparing about a hundred tech workers to find, talk to and videotape homeless people in the vicinity of the Twitter building in midtown San Francisco.

“For safety’s sake, we should go out in pairs. … Have a discussion guide with you, and rehearse so you don’t need to read off it,” Fisher said to the group about to leave the social giant’s refurbished mid-Market Street office building (they were, specifically, in Yammer’s office space). “Ask before videotaping. That said, I tend to ask forgiveness rather than permission. You usually get good results either way.”

He showed the group a short animated film about empathy, and then put up a picture of a safari on the screen.

The divide between tech workers and longtime residents — many of them homeless people and social-services providers — is especially stark in the mid-Market area, where companies like Twitter have established headquarters, thanks to tax breaks from the mayor’s office.

Hoping to ease these conflicts, activists Kyle Stewart and Ilana Lipsett help run ReAllocate, a nonprofit that works to build shared spaces and activities where commuting tech workers and local homeless people can interact.

The Yammer office, in the Twitter building, has a disco-ball light.

At ReAllocate’s “Hacktivation for the Homeless” event last weekend, 12 nonprofits brought their tech needs to engineers to help solve, a pretty standard model for a nonprofit-tech-support event. But this weekend’s happening had a peculiar twist: The hacking paused on Saturday afternoon, and Stewart encouraged the tech workers to venture outside to find and converse with a homeless person — ideally, he said, they would videotape the exchange.

“It’s just the start of a process to connect tech folks with these nonprofit organizations, and then to have them meet the homeless,” said 29-year-old Stewart, who called the videos “visual storytelling to reshape the narrative (that tech workers don’t care about the city’s homeless population).”

Stewart said that he had been couch-surfing with friends for a few months, “so homelessness has become closer to me, personally. I see the stress of having to move on a regular basis.”

Some questions for Stewart: Couldn’t these videos of conversations be viewed as objectifying the homeless subjects?

“Not if we ask, and they say ‘yes.’ At South By Southwest a few years ago, homeless people were turned into hotspots, and everyone was upset, but it was their choice to be hotspots.”

Can you imagine this event being upsetting to people?

“If we’re pissing people off, we’re doing something right.”

The image on the Hacktivation for the Homeless Facebook wall

This brash, novices-know-best approach, lauded in startup culture, sounds jarring when applied to nonprofits and complex issues like homelessness — and some people were upset that the hackathon would be taking place. The event seemed to teeter between effective volunteerism and another way for the tech community to impose its values and tools somewhere they don’t fit. On the event’s Facebook wall, Jim Youll called it “feel good techie yoga” and “a slumber party.”

After the presentation on best practices for conversations with the homeless, Stewart gathered a crowd of 30 or so people. They emerged from the enormous concrete building in staggered clusters, some heading toward Sixth Street, others toward Ellis or Eddy. Stewart ambled down Market Street. He was worried that the rain meant that no one would be out. Soon enough, he walked by a fellow with a shopping cart, and asked him for a light.

Kyle Stewart chatting up Jedi and his friend in the Tenderloin.

As Stewart rolled himself an American Spirit, he chatted with the cart’s owner, Jedi, who asked that no one make a “Star Wars” joke. They talked about the weather (bad) and the neighborhood (decent). Jedi said he was a metalworker and bike repairman, but it had been hard to find work. Stewart told him about Freespace, ReAllocate’s pop-up community center in mid-Market, which offers free bike repairs, and said that they’re always looking for mechanics. Jedi said he’d be interested, and asked how much it pays. Stewart said, unfortunately, it’s all volunteer-run.

Next Stewart walked up to a woman resting by City Hall. He offered her a smoke. She asked him what he was up to and, after he told her, said she wasn’t really that interested in a project.

Stewart rolling a cigarette by City Hall.

Back at Twitter headquarters, Joyride coffee was on tap, and engineers snacked on Belgian waffle cookies, kombucha drinks and raw-nut mixes.

“It’s about fostering a level of empathy between the tech workers, the nonprofits, the homeless,” Lipsett said. “Often, it’s just about creating opportunities for people to interact.”

Karen Gruneisen, associate director at Episcopal Community Services, came because she needed to build a data-collection system to show philanthropists how positive the results were. She admitted that working with technologists was a “pressure-filled issue.”

“Does this help?” Gruneisen said. “It’s not going to make housing costs come down, and I don’t think it’s going to be a salve for folks who want tech companies to invest in the community in proportion to the inequality they create. But from our perspective, we need some help, and they’re offering.”

One young front-end developer wore a zip-up Puma sweatshirt and bright-pink “stunna shades” with horizontal plastic bars on the surface. He said he came to volunteer because he felt pretty strongly about homeless issues — he had lived in homeless shelters as a teenager.

“But a lot of people in tech come from really sheltered backgrounds — 22, and straight out of Michigan,” he said. “It’s scary to them. They don’t even want to look at homeless people ’cause it’s so overwhelming.”

Brandon Croke, 27 and straight out of Ohio, was flown out by a startup and got his first San Francisco apartment at Seventh and Mission, an area with many city-subsidized single resident occupancy (SRO) hotels, which are often the first step up from a homeless shelter. He said he sometimes felt misunderstood by the local community, and that he struggled to find ways to help.

“Hearing what people say about us, it’s like, ‘I’m sorry, an opportunity presented itself, it was a job and I took it.’ I felt really guilty about being a new person here,” Croke said. “And, yeah, it’s a hackathon and we say we’re building an app, but what we’re really trying to build is connection. The words sometimes get in the way.”

Three representatives from Larkin Street Youth, a service program for homeless and traveling kids that is now celebrating its 30th year, sat on brightly colored wraparound couches. They had come because they wanted an app so that their clients could book beds with smartphones, which they said almost all their clients had all or some of the time. Zendesk and the St. Anthony Foundation also recently collaborated on an app for homeless people to search for services.

“At first, we were like, mobile app? Do we need a mobile app? But we need to meet the kids where they are. All of them have access to computers sometimes or all of the time. Today, 95 percent of how we interact with our clients is face to face, and we want to be able to expand,” said outreach counselor Eva Kersey. “We got here, and [the engineers] just started building something right away.”

Kersey and the Larkin Street team hadn’t known that the event would include a walking tour, but said it might be a good idea.

“It might be good to help these guys get over their fear,” said Katherine Tom, assistant manager at Larkin Street Youth. “A lot of the them are afraid of homeless people.”

Here’s the video one hackathon participant, Josh Wolf, uploaded of his conversation with a woman named Gypsy:

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